The Secret to Making Impossible Decisions

Decisions, decisions, decisions. So many of them come down to two genuinely good options. No clear winner, no obvious loser, just two different paths. And when that happens, we end up spending enormous amounts of time and energy building pro and con lists, running through every possible scenario, and living entirely in our heads trying to figure out the "right" answer.

What I want to offer you today is a different way to approach decision-making. Because the longer you stay in indecision, the more it costs you. Your mental bandwidth, your energy, and your ability to actually move forward. Indecision keeps you in survival mode.

Why Most Career Decisions Aren't as Simple as a Pro/Con List

Here's the thing: most career decisions aren't between a good option and a bad one. Let's say you have an offer to move into a new role in a new city. It comes with a great title, a promotion, more money, and a real opportunity for growth, but it also means leaving your extended family and the community you've built over the years. You're stuck.

A pro and con list is one way to evaluate the options, and sometimes that's genuinely all you need. Another useful tool is the regret minimization framework which means asking yourself what you'd regret more when you're 80. I use that one a lot, especially when I've taken some of the bigger leaps in my own career. Telling myself I would regret it if I didn't try this has helped me move forward more than once.

But sometimes, even after all of that, you're still stuck. And that's because the real question isn't about logic at all. It's about which choice aligns with who you are, and who you're becoming. You can't find that answer in a spreadsheet.

What Your "Gut Feeling" Is Actually Telling You

You might look at an opportunity that's perfect on paper and still feel a quiet sense of dread about taking it. Something's off, but it's hard to name exactly what. That's where values come in.

Values are the internal boundaries that define what adds to your wellbeing versus what drains it.

Here's a concrete example: if autonomy is a core value for you, taking a high-paying role with no control over your schedule or your work is going to create misalignment. No matter how great it looks from the outside, no matter how much money is involved, you're going to be miserable.

That sinking feeling, that sense that your intuition is off? That's your values talking to you.

Values are also relatively consistent over time, which makes them a reliable compass. What matters deeply to you now is very likely going to matter to you in the future. Naming those values consciously, actually putting words to them, is what allows you to use them as a decision-making tool. They tell you which trade-offs you can genuinely live with, and which ones will slowly drain you.

I'll be honest: there have been times in my own life where I've ignored that internal whisper. I've overridden my values and taken the thing that looked good on paper, and I did learn a lesson from that. Not listening to yourself has a cost.

How to Actually Make a Values-Based Decision

This is where the magic happens. Instead of using logic alone, you add a layer of values on top, and decision-making shifts from endless overthinking to evaluating choices through an alignment lens.

Here's how to do it:

Step 1: Identify your top three to five values. This can be harder than it sounds. When you look at a list of values, you'll want to claim all of them. Resist that urge. Push yourself to prioritize and get it down to three to five that are truly most important to you.

Step 2: Rank them by weight. Not all of your values carry the same importance. Some are non-negotiables (like the autonomy example above), and some are nice-to-haves. Maybe creativity is important to you, but it's something you're willing to set aside in your professional life because you can fulfill it elsewhere. Know which is which.

Step 3: Run your decision through the filter. Now that you know your top values and how they rank, you can evaluate your options against them in a structured way.

Seeing It in Action: The Promotion Dilemma

Let's walk through an example. A promotion offers real growth opportunities and financial gain — genuinely good things. But it also means longer hours, more travel, and less time with your family. Your current role, meanwhile, gives you work-life balance.

When you run this through your values filter, the answer becomes clearer. If growth is your highest-ranked value right now, the promotion is probably your most aligned choice, even with the trade-offs. But if connection and stability are weighted higher, staying in your current role is likely to serve you better, even if it feels like you're passing something up.

You can value both growth and connection. But to make a decision, one has to take priority.

What If You Choose Wrong?

This is the fear that comes up every single time, so let's address it directly: there is no "right" or "wrong" choice here. There is no perfect choice. The best choice is the one that aligns most with who you are right now.

That doesn't mean it will be easy. But it does mean the hard parts will feel worth it, because they're in service of something that actually matters to you, and you'll know exactly why you made the decision you made.

Will you still have moments of doubt? Probably. You might not know for years whether it was the "right" call. But what you won't have when you make a values-aligned choice is that pit in your stomach telling you you're living out of alignment. You won't be second-guessing yourself on why you chose what you chose.

And I get it. The fear of making the wrong choice is very real. But here's what I need to remind you: you have navigated hard things before. You've made decisions without knowing how they'd turn out, and you handled it. You got through it. This time won't be any different.

The cost of waiting for certainty is far higher than making an aligned choice and adjusting as you go.

A Reframe to Take With You

Instead of asking "What if this goes wrong?" try asking: "What if I trust myself to handle the outcome?"

Because you will. You'll figure it out. You always have, and you always do.

You're choosing between two paths, and you're going to make either one of them work. The difference is that one of those paths aligns more with your values. And when you choose with that alignment in mind, even when things get hard, especially when things get hard, you're choosing to lead your life instead of just surviving it.

My Own Experience: Choosing Alignment Over Comfort

A while back, I made the decision to change careers and go back to school, spending significant time and money when, by most measures, things were going just fine where I was. But deep down, I knew I wanted a career that was more aligned with my core values: connection, helping people, and continuous learning. That's what led me to make the pivot.

It has not been easy. But I sleep very well at night knowing it was the right choice for me.

I'd love to hear how you've used values in your own decision-making, or if there are other strategies you rely on when you're facing a tough choice. Drop them in the comments below.